CA2022897C - Cyclopropanethiocarboxamides - Google Patents

Cyclopropanethiocarboxamides Download PDF

Info

Publication number: CA2022897C
Authority: CA; Canada
Prior art keywords: alkyl; formula; set forth; compounds; weight
Prior art date: 1989-08-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA002022897A

Other languages

English (en)

French (fr)

Other versions

CA2022897A1 (en

Inventor

Uwe Kardorff

Joachim Leyendecker

Hans-Juergen Neubauer

Christoph Kuenast

Peter Hofmeister

Wolfgang Krieg

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-08-10

Filing date

1990-08-08

Publication date

2002-03-26

1990-08-08 Application filed by BASF SE filed Critical BASF SE

1991-02-11 Publication of CA2022897A1 publication Critical patent/CA2022897A1/en

2002-03-26 Application granted granted Critical

2002-03-26 Publication of CA2022897C publication Critical patent/CA2022897C/en

2010-08-08 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

IIPJWNFOLPDTEQ-UHFFFAOYSA-N cyclopropanecarbothioamide Chemical class NC(=S)C1CC1 IIPJWNFOLPDTEQ-UHFFFAOYSA-N 0.000 title claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000000575 pesticide Substances 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims description 8
241000607479 Yersinia pestis Species 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
KLVURCLPBORFSV-UHFFFAOYSA-N cyclopropanecarbodithioic acid Chemical compound SC(=S)C1CC1 KLVURCLPBORFSV-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 26
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 27
239000000203 mixture Substances 0.000 description 15
-1 vitro Chemical class 0.000 description 14
238000002474 experimental method Methods 0.000 description 11
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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238000009472 formulation Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
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AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
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FTPCUGHCFKLABN-UHFFFAOYSA-N n-[2-(4-phenoxyphenoxy)ethyl]cyclopropanecarboxamide Chemical class C1CC1C(=O)NCCOC(C=C1)=CC=C1OC1=CC=CC=C1 FTPCUGHCFKLABN-UHFFFAOYSA-N 0.000 description 1
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/46—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Detergent Compositions (AREA)

CA002022897A 1989-08-10 1990-08-08 Cyclopropanethiocarboxamides Expired - Lifetime CA2022897C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3926468A DE3926468A1 (de)	1989-08-10	1989-08-10	Cyclopropanthiocarbonsaeureamide
DEP3926468.8		1989-08-10

Publications (2)

Publication Number	Publication Date
CA2022897A1 CA2022897A1 (en)	1991-02-11
CA2022897C true CA2022897C (en)	2002-03-26

Family

ID=6386887

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002022897A Expired - Lifetime CA2022897C (en)	1989-08-10	1990-08-08	Cyclopropanethiocarboxamides

Country Status (8)

Country	Link
US (1)	US5132326A (de)
EP (1)	EP0412391B1 (de)
JP (1)	JP2806439B2 (de)
KR (1)	KR0177809B1 (de)
AT (1)	ATE95172T1 (de)
CA (1)	CA2022897C (de)
DE (2)	DE3926468A1 (de)
ES (1)	ES2059928T3 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW201727B (de) *	1991-05-20	1993-03-11	Sumitomo Chemical Co

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS52128220A (en) *	1976-04-20	1977-10-27	Ishihara Sangyo Kaisha Ltd	Herbicides
US4625048A (en) *	1982-08-13	1986-11-25	Hoffmann-La Roche Inc.	Carbamic acid esters
DE3628082A1 (de) *	1986-08-19	1988-03-03	Basf Ag	Carboxamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen
DE3823521A1 (de) *	1988-07-12	1990-02-15	Basf Ag	Cyclopropancarboxamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen

1989
- 1989-08-10 DE DE3926468A patent/DE3926468A1/de not_active Withdrawn
1990
- 1990-07-30 ES ES90114590T patent/ES2059928T3/es not_active Expired - Lifetime
- 1990-07-30 DE DE90114590T patent/DE59002904D1/de not_active Expired - Lifetime
- 1990-07-30 EP EP90114590A patent/EP0412391B1/de not_active Expired - Lifetime
- 1990-07-30 AT AT90114590T patent/ATE95172T1/de not_active IP Right Cessation
- 1990-07-30 JP JP2199362A patent/JP2806439B2/ja not_active Expired - Lifetime
- 1990-08-02 US US07/561,613 patent/US5132326A/en not_active Expired - Lifetime
- 1990-08-08 CA CA002022897A patent/CA2022897C/en not_active Expired - Lifetime
- 1990-08-10 KR KR1019900012281A patent/KR0177809B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH03135953A (ja)	1991-06-10
ATE95172T1 (de)	1993-10-15
DE59002904D1 (de)	1993-11-04
KR910004558A (ko)	1991-03-28
EP0412391B1 (de)	1993-09-29
CA2022897A1 (en)	1991-02-11
KR0177809B1 (ko)	1999-05-15
JP2806439B2 (ja)	1998-09-30
EP0412391A1 (de)	1991-02-13
US5132326A (en)	1992-07-21
DE3926468A1 (de)	1991-02-14
ES2059928T3 (es)	1994-11-16

Legal Events

Date	Code	Title	Description
1997-08-25	EEER	Examination request
2010-08-08	MKEX	Expiry

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